Transforming the masculine form into something feminine is both the literal and metaphorical equivalent of “putting lipstick on a pig”. It takes talent, dedication,and the hard work of those in sweatshops worldwide to make it event remotely believable.

It all depends on what you’re going for, so as always, don’t take my advice as gospel, by all means do your own thing. Some folks are happy with being a hairy pantie boy, while others (myself included) want to see how well they can mimic the female form. This is my journey, take what you need then go your own way. This also isn’t a post about body shaming, everyone has something different in mind for their ideal body and there is no one ideal body type… this is about your decisions to create the body you want.

Thongs are a horrible choice in underwear if you have man parts. Unless you purchase a male-specific thong, your shit is going to be dangling to one side or the other all day. They look great on your ass, but if you want something that you can wear comfortably and look good in on both sides at once, go with something lace and cheeky. The lace gives enough stretch for your package to fit while the cheeky gives you all the benefits of a thong (highlighting and dividing your ass cheeks). Here are some of my favorites:

Shapewear is a girl’s best secret. You have two options with shapewear. You can get something that trains your body long-term or you can go with something that gets everything pushed into the right place for your outfit. I’m actually a fan of both.

Latex corsets offer a good option to shape instantaneously while producing lasting results. I wear mine for around 6 hours a day and have seen positive results.

Charmian Women’s Leopard Latex Underbust – These things are oddly comfortable. Make sure to read up on the sizing (and for god’s sake measure yourself with a cloth tape measure). I’d also recommend going ahead and buying your size and the next size down; I realized really fast results and had to wait on the smaller size.

Body suits are another great option. With the right bodysuit/corset combination, you’ll be able to create killer body that performs in even the most demanding, form-fitting clothing.

One of my biggest mistakes early on in dressing was letting the male me trying to influence my bra and fake boob selection. Sure bigger is better, but it’s also harder to manage and can make finding the right clothes a chore. Ultimately, I’ve backed off that approach and toned it down to a “B” cup. I really love Smart and Sexy’s pushup bras because the give the right amount of boob without looking like a floppy, silicone filled disaster.

In my first post, I pointed out that a killer look is a function of finding the right clothes for your body. Personally, I’ve had a luck with skirts and more form fitting clothing, but I have the advantage of being slim and lanky. Don’t commit to any one type of clothing until you really figure out what works for. This goes all the way down to the bra and panties.

Take these tips with a grain of salt, I’m hardly an expert, but I figured if I struggled through the experience to arrive at a decent solution, I should be kind enough to save those embarking on their own journey some time and trouble. That being said, my first tip… slum the clearance aisle.

If you’re just getting started with gender bending fun, there’s a couple of realities you should acknowledge:

You don’t really know what you’re doing. It’s a harsh reality, but you’ve been dressing and performing in one gender role your entire life. Gender is performance art, but switching it up means learning a whole new set of rules.

You don’t know what works for you. Sizing, colors, cut, it’s all up in the air. You need some trial and error to learn.

Part of the thrill of crossdressing and gender play is having options to work with. One outfit would be boring… lots of outfits gives you room to play.

When I started looking for clothing and makeup, I was shocked at the sticker prices. I didn’t want to shell out tons of cash for items I wasn’t sure about in terms of fit and how they looked on me. I started hitting up stores with slashdown prices and just being liberal in terms of what I was willing to try (Rugged Wearhouse, TJ Maxx, etc.).

I’ve picked up most of my makeup at 70% off or better and I’ve hit several sales where I’ve walked away with clothing pieces for $1-3 each.

What I’ve learned is that using this approach allows me to try something out in a non-judgmental environment and allows me time to experiment with it. Makeup has been a hilarious process of trial and error for me, so I’m glad to have the room to put it on, take it off, and put it on again. I’ve probably blown through 10 pairs of now mangled fake lashes just trying to put the fucking things on.

Clothing has been the same story. Sizing is a bitch and fit is hard to nail when you’re combining pieces to make outfits. I’ve learned what works for my body type and that’s created a lot more confidence for me. You can of course catch some of my awesome clothing steals on my Instagram feed.

Hi there, I’m Josie. Thanks for stopping by and thanks for your patience as I start building the site out. I started playing with crossdressing a short time ago; this site follows along as I continue that journey and hopefully provides some assistance for those questioning their own gender identity.

Check me out on Instagram or Twitter. Thanks for stopping by and check back often. My goal is to share whatever tips I figure out and any good products I can point you to. I also occassionally plan to share my insights on the unsolicited dick pics I receive via social media.